Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 109 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
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Hawaii
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Superb961 reviews4.9
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....
Kauai’s Na Pali Coast Snorkel and Sail Tour
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More
Likely to Sell Out Kauai’s Na Pali Coast Snorkel and Sail Tour
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Hawaii
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Superb568 reviews4.8
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More
Likely to Sell Out Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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Hawaii
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Superb841 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Paragon Lahaina Sunset Sail
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More
Likely to Sell Out Paragon Lahaina Sunset Sail
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Hawaii
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Superb18 reviews4.8
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....
Likely to Sell Out Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor
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Hawaii
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Superb20 reviews4.6
Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, ....
Waikoloa Signature Catamaran Sunset Sail
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More
Likely to Sell Out Waikoloa Signature Catamaran Sunset Sail
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Hawaii
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Superb413 reviews4.7
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....
Day's End Cocktail Sunset Sail
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More
Likely to Sell Out Day's End Cocktail Sunset Sail
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Hawaii
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Superb87 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More
Likely to Sell Out Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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Hawaii
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Superb308 reviews4.8
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
Kona Tradewind Catamaran Day Sail
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More
Likely to Sell Out Kona Tradewind Catamaran Day Sail
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Hawaii
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Superb47 reviews4.8
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More
Likely to Sell Out Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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Hawaii
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Superb966 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
Likely to Sell Out
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More
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Likely to Sell Out Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
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Hawaii
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Superb208 reviews4.9
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
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Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, and ocean lovers, this Lahaina adventure combines a... More
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Likely to Sell Out Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
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Hawaii
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Superb103 reviews4.9
Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury ....
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Molokini Snorkel and Performance Sail: Mā’alaea Harbor
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More
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Likely to Sell Out Molokini Snorkel and Performance Sail: Mā’alaea Harbor
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Hawaii
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Superb220 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
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Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More
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Likely to Sell Out Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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Hawaii
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Superb58 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
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Snorkel with Manta Rays Guaranteed
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More
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Likely to Sell Out Snorkel with Manta Rays Guaranteed
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Hawaii
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Superb751 reviews4.8
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....
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Waikiki Fireworks Cocktail Cruise
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to remember.... More
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Likely to Sell Out Waikiki Fireworks Cocktail Cruise
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Hawaii
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Exellent8 reviews4.5
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....
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Sunset Cocktail Cruise on our Sailing Catamaran
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More
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Likely to Sell Out Sunset Cocktail Cruise on our Sailing Catamaran
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Hawaii
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Superb64 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....
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2-Hour Oahu Sunset Catamaran Sail
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for ... More
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Likely to Sell Out 2-Hour Oahu Sunset Catamaran Sail
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Hawaii
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Superb134 reviews4.8
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran fr....
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Sunset and Manta Ray Snorkel Adventure
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays! Upon arriving, receive an in... More
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Likely to Sell Out Sunset and Manta Ray Snorkel Adventure
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Hawaii
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Superb864 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....
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Waikiki Sunset Cruise from Oahu
Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More
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Likely to Sell Out Waikiki Sunset Cruise from Oahu
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Hawaii
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Superb66 reviews4.7
Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....
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